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Cheap flights from Chicago Midway Airport to San José from $111

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago Midway Airport to San José departing on 8/9. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Find the cheapest flights from Chicago Midway Airport to San José

Cheap round-trip flights

Southwest Logo
9:10 am - 6:55 pmMDW-SJO
10h 45m1 stop
Southwest Logo
8:50 am - 6:25 pmSJO-MDW
8h 35m1 stop
$366Southwest
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Tue, Aug 19 - Wed, Aug 27
Southwest Logo
6:15 am - 12:45 pmMDW-SJO
7h 30m1 stop
Southwest Logo
8:50 am - 10:25 pmSJO-MDW
12h 35m2 stops
$370Southwest
Find Deal
Tue, Aug 19 - Wed, Aug 27
Southwest Logo
6:25 am - 6:55 pmMDW-SJO
13h 30m1 stop
Southwest Logo
8:50 am - 6:25 pmSJO-MDW
8h 35m1 stop
$387Southwest
Find Deal
Wed, Sep 3 - Wed, Sep 10
Southwest Logo
11:25 am - 6:55 pmMDW-SJO
8h 30m2 stops
Southwest Logo
8:50 am - 10:25 pmSJO-MDW
12h 35m2 stops
$391Southwest
Find Deal
Wed, Sep 3 - Wed, Sep 10
Logo
10:51 am - 10:32 amMDW-SJO
24h 41m1 stop
Logo
11:27 am - 8:22 amSJO-MDW
19h 55m1 stop
$403
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Sat, Aug 23 - Sat, Aug 30
Logo
6:00 am - 11:14 amMDW-SJO
30h 14m2 stops
Logo
11:37 am - 7:33 amSJO-MDW
18h 56m1 stop
$413
Find Deal
Thu, Sep 25 - Sun, Sep 28
Frontier Logo
6:00 am - 1:36 pmMDW-SJO
7h 36m1 stop
Frontier Logo
2:37 pm - 11:05 pmSJO-MDW
8h 28m1 stop
$623Frontier
Find Deal
Mon, Dec 22 - Sat, Dec 27
Frontier Logo
6:00 am - 1:36 pmMDW-SJO
7h 36m1 stop
Frontier Logo
2:37 pm - 11:05 pmSJO-MDW
8h 28m1 stop
$682Frontier
Find Deal
Sat, Dec 20 - Sat, Dec 27
Delta Logo
6:00 am - 12:52 pmMDW-SJO
6h 52m1 stop
Delta Logo
7:00 am - 9:44 pmSJO-MDW
14h 44m1 stop
$689Delta
Find Deal
Sun, Nov 9 - Sun, Nov 16
Delta Logo
6:00 am - 12:52 pmMDW-SJO
6h 52m1 stop
Delta Logo
2:17 pm - 9:44 pmSJO-MDW
7h 27m1 stop
$690Delta
Find Deal
Sun, Nov 9 - Sun, Nov 16

Southwest flights from Chicago Midway Airport to San José, San José Province

Our best Southwest deals on Chicago Midway Airport to San José, San José Province flight tickets
Southwest
Aug 19
MDW9:10 amChicago Midway
10h 45m
1 stop
SJO6:55 pmSan José Juan Santamaria Intl
Aug 27
SJO8:50 amSan José Juan Santamaria Intl
8h 35m
1 stop
MDW6:25 pmChicago Midway
$366
Find similar
Southwest
Aug 19
MDW6:15 amChicago Midway
7h 30m
1 stop
SJO12:45 pmSan José Juan Santamaria Intl
Aug 27
SJO8:50 amSan José Juan Santamaria Intl
12h 35m
2 stops
MDW10:25 pmChicago Midway
$370
Find similar
Southwest
Sep 3
MDW6:25 amChicago Midway
13h 30m
1 stop
SJO6:55 pmSan José Juan Santamaria Intl
Sep 10
SJO8:50 amSan José Juan Santamaria Intl
8h 35m
1 stop
MDW6:25 pmChicago Midway
$387
Find similar

Delta flights from Chicago Midway Airport to San José, San José Province

Our best Delta deals on Chicago Midway Airport to San José, San José Province flight tickets
Delta
Nov 9
MDW6:00 amChicago Midway
6h 52m
1 stop
SJO12:52 pmSan José Juan Santamaria Intl
Nov 16
SJO7:00 amSan José Juan Santamaria Intl
14h 44m
1 stop
MDW9:44 pmChicago Midway
$689
Find similar
Delta
Nov 9
MDW6:00 amChicago Midway
6h 52m
1 stop
SJO12:52 pmSan José Juan Santamaria Intl
Nov 16
SJO2:17 pmSan José Juan Santamaria Intl
7h 27m
1 stop
MDW9:44 pmChicago Midway
$690
Find similar
Delta
Oct 5
MDW6:00 amChicago Midway
7h 08m
1 stop
SJO12:08 pmSan José Juan Santamaria Intl
Oct 18
SJO1:13 pmSan José Juan Santamaria Intl
7h 31m
1 stop
MDW9:44 pmChicago Midway
$701
Find similar

See travel insights to San José from

How to get the cheapest flight ticket from Chicago Midway Airport to San José, San José Province

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest month to fly to San José, San José Province?

The month of August is, on average, the cheapest month to fly to San José, San José Province from Chicago Midway Airport, with most prices found around $456. If you’re not able to fly to San José, San José Province in August, then September is your next best option. Flight prices from Chicago Midway Airport to San José, San José Province during September average around $552.

What is the cheapest day to depart on your flight to San José, San José Province?

The cheapest day to depart from Chicago Midway Airport to San José, San José Province is on a Tuesday when prices can be found for as low as $581. The most expensive day to fly to San José, San José Province is Saturday, with ticket prices averaging around $820.

What is the cheapest time of day to depart on your flight to San José, San José Province?

In the evening is the cheapest time of day to fly from Chicago Midway Airport to San José, San José Province when you can find flight prices for as low as $453. Flying to San José, San José Province in the evening is an ideal time because this is during off-peak travel hours. In the morning is when there is more demand to fly to San José, San José Province, so prices are often more expensive at around $769 per ticket.

When to book flights from Chicago Midway Airport to San José, San José Province

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago Midway Airport to San José, San José Province according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Chicago Midway Airport to San José, San José Province (MDW to SJO) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago Midway Airport to San José, San José Province

Best Price Found

$111

Fastest flight time

6h 35m

Direct flights

None

Airports in San José, San José Province

1 airport
The best one-way flight to San José, San José Province from Chicago Midway Airport in the past 72 hours is $111. The best round-trip flight deal from Chicago Midway Airport to San José, San José Province found on momondo in the last 72 hours is $366.
The fastest flight from Chicago Midway Airport to San José, San José Province takes 6h 35m
There are no direct flights from Chicago Midway Airport to San José, San José Province. Popular non-direct route for this connection is Chicago Midway Airport - San José Juan Santamaria Intl Airport.
There is 1 airport near San José, San José Province: San José Juan Santamaria Intl (SJO)
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  • How far is Chicago Midway to San José Juan Santamaria Intl by plane?

    A flight from Chicago Midway to San José Juan Santamaria Intl will travel around 2210.5 mi. Typically, this will take 6h 35m by plane in normal conditions.

  • When did momondo last update prices for flights from Chicago Midway Airport to San José Juan Santamaria Intl Airport?

    Prices for flights from Chicago Midway Airport to San José Juan Santamaria Intl Airport are updated daily.

  • How many operators does momondo search for flights from Chicago Midway Airport to San José Juan Santamaria Intl Airport?

  • How old do you have to be to fly from Chicago Midway Airport to San José Juan Santamaria Intl Airport?

    The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Chicago Midway Airport to San José Juan Santamaria Intl Airport.

  • What documentation or ID do you need to fly to San José Juan Santamaria Intl Airport?

    The travel and health documents you'll need for your trip to San José Juan Santamaria Intl Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at San José Juan Santamaria Intl Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

  • What is the most popular airline from Chicago Midway Airport to San José, San José Province?

Best airlines flying from Chicago Midway Airport to San José, San José Province

Compare and see reviews for airlines that fly from Chicago Midway Airport to San José, San José Province with momondo
Airline
Rating
Free Cancellation
Price
SouthwestPriceFrom $477Free CancellationRating
8.0
4,250 reviews
Search Southwest flights
DeltaPriceFrom $544Free CancellationRating
8.0
7,952 reviews
Search Delta flights

Traveling to a place near San José?

Book flights to San José if you plan to visit one of these locations
Manuel Antonio
Jacó
Alajuela
Monteverde
Heredia
Dominical
Santa Elena
Esterillos Este

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to San José?

Finding the right flight to San José from Chicago is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to San José quick and easy, saving you time and money.

Can I find flights from Chicago to San José with flexible booking policies on momondo?

All flight searches from Chicago to San José on momondo can be filtered to show those which offer flexible booking policies.

How can momondo help me find flights from Chicago to San José?

momondo provides multiple filters to help you find the best flight to San José from Chicago. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

I’m not ready to book a flight from Chicago to San José right now. Can momondo alert me if prices change?

Of course. momondo tracks the price of Chicago to San José flights. All you need is a valid email address and we will do the rest; it is that quick and easy.

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